1073
Table II. Chemical and spectral data of compounds 3, 4 and 5.
Compound
R
Pyr
Yield
(%)
M.p. (°C)
IR (Nujol)
1H-NMR (DMSO-d6 /TMS) δ (ppm)
(recryst. solvent) ν (cm–1
)
3a
4a
H
H
2-pyridyl 42
3-pyridyl 55
168–169
(Benzene)
164–165
3 050, 1 610, 4.74 (s, 2H, CH2), 6.64 (s, 1H, CH), 6.93–7.81 (m, 10H, Ar), 8.54
1 590, 1 540 (s, 1H, NH), 8.63 (m, 3H, Py)
3 180, 3 030, 4.81 (s, 2H, CH2), 6.75 (s, 1H, CH), 6.93–8.62 (m, 13H, Ar), 8.68
1 615, 1 600, (s, 1H, NH)
1 550
(2-PrOH)
5a
5b
4c
5c
4d
5d
4e
5e
4f
H
4-pyridyl 63
4-pyridyl 48
3-pyridyl 57
4-pyridyl 59
3-pyridyl 64
4-pyridyl 56
3-pyridyl 68
4-pyridyl 67
3-pyridyl 50
4-pyridyl 52
3-pyridyl 72
4-pyridyl 60
3-pyridyl 60
4-pyridyl 50
190–191
(Benzene)
162–163
(Toluene)
124–125
(Toluene)
174–175
(Toluene)
152–153
(Toluene)
159–160
(Toluene)
134–135
(Toluene)
129–130
(Toluene)
137–138
(Toluene)
157–158
(Toluene)
123–124
(Toluene)
129–130
(Toluene)
173–174
(Toluene)
184–185
3 070, 1 620, 4.80 (s, 2H, CH2), 6.69 (s, 1H, CH), 6.93–8.64 (m, 13H, Ar), 8.71
1 595
(s, 1H, NH)
2-CH3
3-CH3
3-CH3
4-CH3
4-CH3
2-OCH3
2-OCH3
3-OCH3
3-OCH3
4-OCH3
4-OCH3
2-Cl
3 360, 3 020, 2.13 (s, 3H, CH3), 4.81 (s, 2H, CH2), 6.70 (s, 1H, CH), 6.83–8.64
1 620, 1 590 (m, 13H, Ar + NH)
3 060, 1 610, 2.24 (s, 3H, CH3), 4.81 (s, 2H, CH2), 6.78 (s, 1H, CH), 6.80–8.68
1 540 (m, 13H, Ar + NH)
3 060, 1 620, 2.23 (s, 3H, CH3), 4.79 (s, 2H, CH2), 6.70 (s, 1H, CH), 6.78–8.65
1 540 (m, 12H, Ar), 8.71 (s, 1H, NH)
3 020, 1 620, 2.19 (s, 3H, CH3), 4.77 (s, 2H, CH2), 6.74 (s, 1H, CH), 6.86–8.74
1 600, 1 540 (m, 13H, Ar + NH)
3 060, 1 620, 2.22 (s, 3H, CH3), 4.78 (s, 2H, CH2), 6.70 (s, 1H, CH), 6.88–8.66
1 560 (m, 12H, Ar), 8.72 (s, 1H, NH)
3 080, 3 020, 3.74 (s, 3H, CH3), 4.80 (s, 2H, CH2), 6.79 (s, 1H, CH), 6.87–8.65
1 630, 1 590
(m, 13H, Ar + NH)
1 630, 1 600
3.72 (s, 3H, CH3), 4.76 (s, 2H, CH2), 6.71 (s, 1H, CH), 6.83–8.64
(m, 13H, Ar + NH)
3 160, 3 060, 3.66 (s, 3H, CH3), 4.79 (s, 2H, CH2), 6.51–9.13 (m, 14H, Ar +
1 640, 1 590 NH + CH)
5f
3 140, 3 080, 3.66 (s, 3H, CH3), 4.79 (s, 2H, CH2), 6.70–8.63 (m, 13H, Ar +
1 620, 1 600 CH), 8.71 (s, 1H, NH)
4g
5g
4h
5h
3 150, 3 020, 3.67 (s, 3H, CH3), 4.75 (s, 2H, CH2), 6.75 (s, 1H, CH), 6.83–8.64
1 620, 1 580 (m, 12H, Ar), 8.67 (s, 1H, NH)
3 100, 1 630, 3.65 (s, 3H, CH3), 4.73 (s, 2H, CH2), 6.68 (s, 1H, CH), 6.81–8.64
1 620, 1 595 (m, 12H, Ar), 8.69 (s, 1H, NH)
3 350, 1 630, 4.92 (s, 2H, CH2), 6.78 (s, 1H, CH), 6.95–8.65 (m, 13H, Ar + NH)
1 610, 1 550
2-Cl
3 340, 3 020, 4.90 (s, 2H, CH2), 6.71 (s, 1H, CH), 6.95–8.63 (m, 12H, Ar), 8.68
1 620, 1 590, (s, 1H, NH)
1 540
(Toluene)
4i
5i
4j
3-Cl
3-Cl
4-Cl
3-pyridyl 51
4-pyridyl 67
3-pyridyl 20
139–140
(Toluene)
139–140
(Toluene)
164–165
3 060, 1 620, 4.88 (s, 2H, CH2), 6.76 (s, 1H, CH), 6.96–8.73 (m, 13H, Ar + NH)
1 590, 1 550
3 060, 1 620, 4.88 (s, 2H, CH2), 6.72 (s, 1H, CH), 6.97–8.66 (m, 12H, Ar), 8.74
1 590, 1 540
(s, 1H, NH)
3 100, 3 020, 4.84 (s, 2H, CH2), 6.75 (s, 1H, CH), 7.00–8.62 (m, 12H, Ar), 8.67
1 630, 1 610, (s, 1H, NH)
1 550
(Ethyl acetate)
5j
4-Cl
4-pyridyl 51
3-pyridyl 65
4-pyridyl 62
159–160
(Toluene)
189–190
(2-PrOH)
184–185
(2-PrOH)
1 600, 1 550
4.82 (s, 2H, CH2), 6.69 (s, 1H, CH), 6.99–8.64 (m, 12H, Ar), 8.71
(s, 1H, NH)
4k
5k
4-NO2
4-NO2
1 620, 1 580, 5.04 (s, 2H, CH2), 6.79 (s, 1H, CH), 7.20–8.63 (m, 12H, Ar), 8.74
1 500 (s, 1H, NH)
1 600, 1 580, 5.02 (s, 2H, CH2), 6.73 (s, 1H, CH), 7.19–8.64 (m, 12H, Ar), 8.78
1 540
(s, 1H, NH)
The tested compounds showed activity against myco-
bacteria with MIC values ranging from 6.25 µg/mL to
over 100 µg/mL. MIC values as well as the results of
cytotoxicity assays are reported in table III. The most
active compounds against M. tuberculosis H37Rv were
2d, 2j and 2k (MIC 6.25 µg/ml). However, a significant
activity was also exhibited by compounds 2c, 2f, 2g and
2i (MIC 12.5 µg/mL) and 2b, 2h and 4a (MIC 25 µg/
mL). The most effective compounds in the inhibition of
growth of M. tuberculosis INH-R were 2g, 2j and 2k
(MIC 25 µg/mL). All the tested compounds showed a
higher activity against M. tuberculosis H37Rv than M.